by Craig Higson-Smith and Sabelo Ngwenya
When we first began our mentoring relationship, both of us — one in his fifties, one in their twenties — were unsure what to expect. One of us came from a world of professional networks, stable income, and long years of experience; the other from a background where opportunity is scarce, where side hustles and survival often take the place of formal career paths.
We met through d-lab’s structured mentorship program, but what unfolded went far beyond the professional. It became an experiment in listening across generations, in building trust between people from very different worlds, revealing not only the practical value of mentorship but also its power to connect across generations, classes, and life stories.
Finding Common Ground
Our very first exchange was not promising. The introductory letter Sabelo, the mentee, sent was late and written with heavy help from an AI tool — it read stiff, artificial, and unsure of itself. Craig, the mentor, wondered whether this person actually wanted mentoring, or whether they were just ticking a box.
But the moment we met, everything shifted. Sabelo’s wide smile, easy laughter, and warm curiosity broke the ice instantly. There was chemistry—human, open, and real. From Sabelo’s perspective, there was relief in realizing that Craig wasn’t just another professional figure. “I felt we could connect on things like being queer, mental health, and our thoughts about the planet. We could talk about serious things but still laugh.” Those early meetings were also about testing the limits of privacy that are part of every relationship. Although we shared much common ground personally, there was also a need to have honest, sometimes uncomfortable conversations. As Sabelo reflected; “We found spaces that accommodated each other.”
Trust arrived early, when Sabelo asked a simple but powerful question: “Have you ever had a mentor, and what were the best and worst things about that relationship?” That question leveled the playing field. It allowed Craig to be vulnerable and set a tone of equality rather than status. In return, Sabelo admitted that they had leaned too heavily on AI for that first letter out of fear of not being “good enough.” We learned that honesty would be met with curiosity and respect. From then on, neither of us pretended to have it all figured out.
We set boundaries early — around confidentiality, expectations, and communication — and that structure gave the freedom to explore deeper issues. Over time, trust grew through consistency. We met regularly, spoke frankly, and treated each other’s time seriously.
Breaking out of “mentoring meetings”
Some of our most important engagements happened not during structured sessions, but through a couple of outings. Together we went on informal weekend excursions to art galleries, studios, and creative spaces around the city. For Sabelo, who had always felt drawn to visual art, theatre, film, and all forms of media, these outings were stimulating and offered an opportunity to look at how other creative people are working to make a living, doing something that they love. It was clear that it is difficult for people in the arts to achieve a stable income, but it is not impossible.
For Craig, those outings were just as transformative. “They reminded me that mentorship isn’t only about advice — it’s about shared experience. I got to share something that’s dear to me, and in turn see it through Sabelo’s eyes.” Sabelo has an instinctual love and understanding of visual art and the way contemporary African artists draw on the work of those who have gone before, constantly bringing challenging interpretations and ideas that reflect our rapidly changing world. These weekend outings deepened our working relationship, opened creative horizons, and reminded us both that growth often happens outside structured plans.
Learning from Difference
Mentorship across generations always carries power dynamics. We were acutely aware of ours: one with professional security and privilege, the other navigating uncertainty and the daily pressure on young people earning small sums of money to contribute to their family’s survival before securing their own. In speaking openly about these pressures, something that Sabelo had had few opportunities to do, we observed how a practice rooted in communal care can also prevent young people from building some savings, getting a foothold in life, progressing and ultimately being able to provide more for their families. The balance between caring for one’s family and still planning for the future is very difficult, a balance that many young, black South Africans navigate every day. Without some savings, relatively minor events — the loss of a monthly train ticket or running out of airtime — can result in scarce opportunities being missed or work being impossible to complete.
Through these differences, we learned to approach the world through each other’s lenses: Craig discovering how precarious and competitive youth employment has become, and Sabelo learning how older professionals think, communicate, and make decisions.
Shifting Priorities
Sabelo’s goals evolved over time. They began with a practical dilemma familiar to many young people looking for work: how to balance creative passions with financial survival. Their love for film, theatre and media in all its forms competed with the urgent need for stable work in technology and digital security.
As the months passed, our conversations broadened into professional communication, time management and task prioritization, workplace confidence, and navigating workplace relationships and, eventually, searching for jobs and internships. We moved fluidly between personal and professional worlds, recognizing that they are inseparable. An exciting breakthrough came for Sabelo when they were placed in a position that aligned with their creative side hustle — an internship where passion, learning and the potential for future earning came together.
In the ongoing shifts in our work together, Sabelo introduced Craig to new digital tools, AI shortcuts, and the social media realities of his generation. Craig, in turn, taught Sabelo the foundational skills of professional communication, giving and receiving feedback, how to ask for what one needs without fear, and how to manage expectations.
Moving Forward
A shared learning was the depth of consistency that mentoring required. We met regularly, checked in often, and held each other accountable. That rhythm created momentum and trust.
For Sabelo, mentorship became a mirror: a space to see themself as capable, to bring the best version of himself to work, to take initiative, and to remain enthusiastic about learning new skills. “I’ve learned to always be proactive,” he said. “To take risks, be bold, and carry what I’ve learned within myself.”
For Craig, the rewards were also profound: a renewed sense of relevance, an expanded understanding of how inequality plays out in young lives, and a reminder that listening—deep, patient listening—is sometimes the most valuable gift one can give. “It is easy to lose sight of how much structural luck shapes our paths. Mentoring revealed how steep the climb is for those without that privilege”.
Despite all the growth, the practical challenge remains the same: Sabelo still needs stable, decently paid employment close to the opportunities that match their skills and creativity. For most young South Africans, the gap between potential and opportunity is wide. Mentorship can illuminate the path, but it cannot single-handedly remove the obstacles.
To mentors: start with humility and curiosity. Don’t rush to fix things. Listen deeply and allow yourself to be vulnerable from the beginning. Set clear agreements, meet consistently, and balance structured guidance with unwavering support. Go beyond the formal meetings. Share experiences that bring joy — walks, museums, concerts, coffee shops. Those outings can do more for connection and confidence than any number of scheduled sessions.
To mentees, approach mentoring with enthusiasm, commitment, curiosity and respect. It may seem like older people from very different places in life are irrelevant to your journey, but there is in fact a great deal to learn from people who have had the opportunity to observe and reflect on the changing opportunities and challenges of the working world.
To organizations with mentorship programs: treat mentorship as serious work, provide structure, clarity, and follow-up. Make sure mentors understand confidentiality, boundaries, and expectations. And recognize that the true impact of mentoring is relational, not transactional. It’s not about producing outcomes on a schedule—it’s about enlarging perspective, one conversation at a time.
As we look back, both of us feel changed. Mentorship has become something more like a partnership, a space of growth for two people at different points in life, each learning to see the world through the other’s eyes. The conversations continue, and so does the learning. That, perhaps, is the quiet miracle of mentorship: two lives meeting in good faith, and leaving each other larger than before.